Cheap, chill solo travel for long Labor Day vacation

August 16, 2016 9:48 PM

My vacation plans just disappeared, and I need to put together new ones! This is for one woman over Labor Day weekend on a budget, within the US. Details and goals within.

I'm a 30-year-old woman who lives in NYC, traveling alone. If flying, I prefer Southwest; LaGuardia is super ideal, Newark is also possible. My budget is definitely under $1k for flight + hotel, hopefully under $1k for the entire vacation. The time frame is leaving 9/1-9/3, returning 9/6-9/7.

Goals (in order):
- Swimming! Hotel must have an available pool and hot tub, nonnegotiable. I would love destinations that feature calmer swimming, like lazy river tubing/floating, but not like ocean swimming (I love it, but not comfortable doing it totally alone).
- Food! I'm neither adventurous nor classy, just enthusiastic. My planned vacation was to the South, where I could eat a ton of barbecue, ice cream, and Waffle House; I also love seafood, fried chicken, carbs, etc. Cheap + tasty are the main factors.
- Chilling! I'd like somewhere quiet enough that I don't feel guilty if I spend a day sitting around and knitting or reading poolside. I do want to do cool stuff, this isn't a pure chilling vacation, but I don't want zero chill like NYC. Somewhere not always super crowded would be great.
- tbh probably casual sex one or two nights. I'm not looking to go to Hedonism or anything, it just rules out shared airbnbs.

Neutral:
- I don't drink or smoke pot (or cigarettes). Don't care if others do, but wine tours, dispensaries, etc., aren't a draw for me.
- I don't care if the hotel is super swank as long as it's safe and clean. I do want my own private bedroom and ensuite bathroom, not a hostel, but I don't care if the rooms are tiny.
- For me, Labor Day is just a convenient long weekend, not a major holiday. I'm happy to do related cool stuff if it's there (lobsterfest in Chicago??), but I would also be fine treating it like any other night.

Limitations:
- I have a drivers' license for ID only; I'm so out of practice that I'm not comfortable driving at all, so I would need transport or public transit (or everything within walking distance).
- I've never had a passport of any kind, which rules out international travel. I'm working on getting one for the future, but won't have it in time.
- A cruise sounds kind of ideal, right? but I don't have even a passport card, so can't go to Bermuda, Canada, anywhere. Also, it looks like with the single supplement, cruises are really pricey for solo travelers.

Starter ideas: Southwest currently has sales from LaGuardia to: Atlanta, Chicago (Midway), Dallas (Love), Denver, Houston (Hobby), Indianapolis, Kansas City (MO), Milwaukee, St. Louis. I don't know anyone in any of these cities, and I've never been to any of them.

This will be my first vacation that doesn't revolve around crashing on a friend's couch, so I'm totally unsure about logistics. (I'm not even sure I shouldn't just save the money for something more responsible than travel -- as you can tell, I haven't traveled much.) The more detail you can give, the better, please!

posted by anonymous to Travel & Transportation (6 answers total)

Go to Asheville.
posted by oceanjesse at 10:18 PM on August 16, 2016 [2 favorites]

Yep, sounds like you want a chill little tourist town with good coffee shops and some foodie culture. Memphis (just-outside-of-downtown neighborhoods) or Knoxville, TN, or Louisville, KY (in the hipster-ish neighborhood east of downtown) could also work? (A city might facilitate your last travel goal more easily; the trick is staying in a chill neighborhood.) Asheville, NC is lovely though.
posted by eviemath at 4:07 AM on August 17, 2016 [1 favorite]

I'm 29 and live in NYC and travel by myself a lot. Here are a few random possibilities:
Savannah
Nashville
Austin
Burlington
Portland (Maine, I think west coast might not be worth it for you this trip given timing)
Fire Island (super easy LIRR+ ferry- go to Ocean Beach part)
Mystic
Charlston
Chicago

Have fun!
posted by jenbo1 at 4:30 AM on August 17, 2016

How about Richmond, VA? Fly to Richmond International Airport (RIA), take the bus or taxi to your hotel. Richmond is small enough that you can walk/bus/bike most places you'd want to go over a long weekend (highly recommend bike rental for the freedom to explore at-will). Lots of cool little shops, bars and restaurants in Carytown. Easy access to the James River and lot of companies that will take you rafting, paddleboarding, etc. Virginia Museum of Fine Arts and Lewis Ginter Botanical Gardens are beautiful, and offer numerous spots to just sprawl out and chill on the grounds.
posted by the thought-fox at 7:46 AM on August 17, 2016

I found Chicago VERY do-able. The El train is pretty extensive, there's a ton of cool museums, and there are even beaches in the city on Lake Michigan, and Navy Pier has a cool little boardwalk-y kind of thing going on, what with the ferris wheel. And it's a city and you would be able to find a foodie scene if you wanted one, but you'll definitely be able to find unpretentious food too. The street-cart hotdogs are prepared "Chicago style", with a bunch of extra stuff on them that doesn't usually come on a hot dog that is traditional to Chicago, and I went so crazy for the Chicago-style dogs that I went a full 36-hour period eating nothing BUT hot dogs before noticing it.
posted by EmpressCallipygos at 11:05 AM on August 17, 2016

Oh - and I let a guy in Wicker Park randomly pick me up in a bar, so there you go with the nookie element.
posted by EmpressCallipygos at 11:05 AM on August 17, 2016